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Writer’s Note: I am in the center of a two week streak of real life madness so blogging time took a serious hit. I have been meaning to write this anyway and remove the ancient dead pages with a bibliography and links page – in fact, this post. So while I am crazy busy, here are the books I read/am reading and the podcasts I absorb with all their links and references.

A couple of fine Internet friends asked for a list of books and resources that are gentler than attempting to get through an Economics textbook. I pour data into my head every moment I can – I read an awful lot. When I’m not reading, I’m driving or working. I have a long commute so I listen to a number of podcasts.

Podcasts

I use the Apple Podcast player that comes on the iPhone. To be honest, as a piece of software, it fails where others have succeeded and I cannot recommend it; smarter people have written better better Podcast players than what Apple ships as default on their phone. But because I moved all my Podcasts there when the software was first released I have been stuck with it.

Books

I admit: I don’t read much fiction. I have given up largely on dead tree books and make heavy use of the Kindle. The search and highlight feature has been the most useful feature. All of these books are available from Amazon. Links provided by Goodreads.

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Let’s pretend our band of murder hobos exist in a world with real money instead of the nice, clean, decimal-based and universally exchangeable currency of gold pieces, silver pieces, electrum pieces, etc. etc. Rational, decimal-based currency with a coherent, internal logic is a mid-19th construction at best – the pound sterling wasn’t decimalized until 1971. A universal one-world currency still isn’t a thing; the Euro is the world’s only real cross-state medium of exchange. Don’t believe me? Go to Windsor and get some Canadian quarters and try to put them into an American coke machine.

Money is a shared hallucination and takes many forms – from debt to coin to paper to electronic to giant stone disks. So let’s do a little thought experiment and think about coinage as was for most of history: an imaginary debt construct between two people, localized statehood expressed, in fun circumstances a physical representation of class, and a moderately inconvenient lump of metal. Got it? Great!

Just before we can ask two questions – hey wait! – the murder hobos go under the mountain and kill the dragon.

Question #1: What is worth more: a gold coin hoard or a silver coin hoard?

Given two dragons – a red dragon on a hoard of gold coins and a blue dragon on a hoard of silver coins – and real historical coinage, without melting the hoard down into ingots, which hoard is worth more? Throw out the gold coins are worth 10 silver coins construct and go for the history books.

Answer? It depends.

1. They are roughly equal with the current exchange rates

What is worth more in a medium of 15th century international exchange, the gold Florence florin or the silver English pound sterling? Answer – it depends on the season and where one is geographically in Europe and what the gatekeepers to exchange rates believe that day. Money is an illusion and a mental abstraction; the silver hoard and the gold hoard are equivalent if the coins can be roughly exchanged for each other in an international monetary exchange market or goods of equivalent value. So theoretically they’re equivalent.

How about an extreme edge case. What if the hoard entirely contains the heavily debased kind-of sort-of gold late Byzantine hyperpyron(the dragon took out a city on the Greek coast) and circulating through the murder hobo fantasy Kingdom are Sicilian silver ducats? No shopkeeper in Sicily will accept a hyperpyron but he will greedily take all those ducats. The gold hoard is essentially worthless but the silver ducats are money. The silver hoard is worth spectacularly more than the gold. Sure our murder hobos can melt down the hyperpyron hoard, extract the gold from the lead or nickel, convert it to ingots, and then convert the ingots to silver ducats through a gold seller – or they can have the immediately spendable silver hoard.

Which is worth more? Answer is: it depends on what the coinage is, who is accepting it, and what is the going exchange rate between silver and gold coins.

2. Neither: They are Both Worthless

The dragon slept on the hoard of coins for a thousand years and, in that time, the coins reverted to their base state as lumps of metal. Not physically – the coins are still physically round and roughly coin shaped. However, the coins are no longer in circulation and cannot be exchanged for goods and services. They are not money. To be money, someone else has to price objects for sale in ancient dragon hoard coins.

Imagine this for a moment: you (the reader) unearth in your backyard across a giant chest full of gold doubloons. Two hundred years ago Templar Pirates stumbled into your not-yet neighborhood while being pursued by the Church for their heresies and decided to bury their chest of doubloons (why doubloons? because they are Templar pirates). Now you have a chest full of doubloons. Congratulations! They are round. They are gold. They have portraits of Ferdinand and Isabella. Now, go to Five Guys and exchange a doubloon for a bacon double cheeseburger with the works and a side of cheesy fries.

Yep.

You are the proud owner of a big chest full of inert metal. You have some fascinating options: call in the archeologists to dig up your backyard, melt it down into gold bars (where without questions?), sell it to some dubious goldbug with a commercial on late night TV, find a wealthy and discerning buyer for the doubloons to mystically convert useless metal into money, or rebury the chest. To exchange doubloons to money means finding a buyer. Finding a buyer means a donation, heavy government taxes or sleazy characters and very possibly a high speed car chase.

You know what? Here’s a shovel.

Back to the dragon’s hoard: spending ancient non-circulating coins in gold or silver is like buying a burger with a doubloon – not an acceptable currency for that time or place. Without a forge, a mint, and a way to convert those ancient coins into passable currency or a hoard of dwarven archeologists to take it for a small reward (wait the dwarves have archeologists?), the murder hobos are the proud owners of a large pile of very heavy metal.

3. Neither++: They are Worth Much Worse than Nothing

The murder hobos hire a minor army to pack the coins into cases and cart them out of the cave. And let’s say for the sake of argument that ancient gold coins of dubious denomination still circulate. Great! The murder-hobos are now fabulously wealthy! They spend their coins. They affix coins to hats and walk around with real, physical money sombreros. They hand the local shopkeepers sacks of coins for onions.

Soon, so does everyone else. And by soon, “really quite soon indeed.”

Our murder hobos are engaging in what we will generously call a little quantitative easing. They dump immense sacks of hard cash on to an economy with little coinage in circulation. Now everyone has money! Sacks and sacks of money! So shopkeepers can charge sacks of cash for their goods to make bigger sacks of cash which they now give to others for their rapidly increasing prices!

And soon it’s all worthless.

Too much unexpected money washes around in the monetary supply. Prices hike. People buy bread with wheelbarrows full of gold dragon coins. Hyper-inflation soars. Economies crash. Poverty prevails. The kingdom collapses. Nearby kingdoms invade. Vicious barbarians behead Good and Wise Kings. Empires disappear to never reappear again. The Age ends and turns to darkness!

Society reverts to a crushing dystopian Mad Max-like existence full of roving bands of murders. Good news for the murder hobos: XP! XP!

Later another dragon collects all the forgotten coins together, stuffs it into the cave, and sits on it.

As a historical reference: after a 1100 year period of hardly any good minting metals except what societies imported from overseas (fall of Rome – 1550AD), Spain enslaved the Native Indians of Peru and forced them to mine vast supplies of gold and silver. The Conquistadors sent it home on giant ships heavy with ingots. The Spanish mint promptly minted this stuff into doubloons, dumped it into the economy and caused Europe-wide 300% inflation. Western Europe went into a depression. Templar Pirates buried cases of it in your backyard.

And so it goes.

Now that we’ve established that perhaps taking cases of gold out of a dragon’s hoard out of a cave and dumping it whole scale on an economy might not be wise…

Question #2: How do the murder hobos liquidate all this filthy lucre?

We’re not going to stop the murder hobos from killing dragons. It’s already happened. It’s the past. There was a quest! And honor! And evil to vanquish!

So how do the murder hobos get rid of this huge pile of likely worthless, possibly dangerous, and certainly gold-colored coinage? After all, the dragon is dead. The money is all theirs if they can do something with it. Some ideas…

1. Go colonize the locals like the Conquistadors and establish a kingdom

If the band of friendly murder hobos can get the coins out of the cave, avoid spending the money like wild monkeys on a bender (no the wizard cannot buy that tower just because), cart it thousands of miles until they find the last reclaimed area of their world – assuming such a thing exists – fight off endless bandits and attacks, level a bunch of times, find a place on some wind beaten mountainous frontier, murderize the locals, and build a stronghold, they can establish a frontier kingdom with the dragon hoard as their base currency. Of course, this new frontier kingdom – missing all the amenities of home like identify kiosks and fairs to trade magic items and bathrooms – are on the ancient dragon hoard standard. Unless the murder hobos want to contend with a highly restricted monetary supply limited by their hoard, never have enough money to pay for an army to go to war to defend their kingdom from the peaceful ork society they kicked off their ancestral holy land, or be able to expand, they’re going to need gold mines. They are going to need to build a mint.

So the murder-hobos use the old dragon hoard to make a newer hoard by forcing the locals to build their infrastructure. They slowly phase out the old dragon hoard base until their new kingdom is on their own currency. The old dragon hoard reverts back to uselessness. Then they stash the old useless coins in a cave near their kingdom. A dragon comes along and sits on it. A new group in the far off future find it and begin the cycle anew. Thus the infinite cycle of murder hoboing marches onward.

Meanwhile, the murder hobos have a kingdom to build and rule on their dangerous frontier with an unshakable Lawful Evil iron fist. They need trade routes and a standing military and a way to purge the land of the locals while establishing their own farming communities and impressing their own serfs into feudalistic service. They need stability. Each takes a piece to control for themselves. The murder hobos have no time to adventure anymore because now they are busy playing a game of highly morally dubious Age of Empires.

2. Liquidate it through mercenaries

One group of people will take that dragon hoard off the murder hobo hands: mercenaries. Sure they’re evil and scum and villainy. And maybe the Paladin complains a little like she does whenever the party starts waltzing down the neutral evil path. But mercenaries don’t care. They will take any hoard in any denomination from any country and turn that money magically from metal into whole scale killing. Mercenaries practice their own version of alchemy.

Sure the mercenaries will take the money off the murder hobo’s hands for free no questions asked but that is such a waste. The murder hobos worked hard for this hoard. A dragon, a thinking, reasoning, intelligent being with opinions and family and hobbies and quite possibly a voting record, died so murder hobos could hire these mercenaries. And that dragon cave hanging over that peaceful peasant village is central to a big, peaceful fantasy kingdom with a complete functional infrastructure including roads and villages and peasants and farms and gold mines and mints and bathrooms. No one needs to travel anywhere. No orks need to be kicked off their ancestral homeland. Nothing needs building. The Paladin can avoid the bigger moral questions. Property really is the best way to liquidate a dragon’s hoard and turn metal into a thing. Possessing the Kingdom wholesale is the quickest way to turn these remaining dragon hoard coins into money.

At this point we inform the Paladin that Lawful Evil is a perfectly valid Paladin alignment. It’s okay. Hugs?

After the murder-hobos obliterate the Kingdom’s army (they never saw it coming from their trusted heroes), imprison the old King, and ennoble several sleazier Mercenary Captains for their service, they must figure out who is going to rule and over what. Someone has to rule their Peaceful Fantasy Kingdom now they’ve gone and conquered it.

– The Fighter sees this as an opportunity to continue the old traditions and crown himself King.

– The Cleric wants to establish a Theocracy under the Gods of Goodness and Light – what could be better than a Kingdom ruled by the One Good Church?

– The Sorceress suggests a charismatic dictatorship under her as a Dark and Beautiful Queen.

– The Wizard, sensibly, suggests a dark oligarchy Star Chamber where they rule as equals in complete secret.

– The Bard, pleading for sanity, starts writing a Constitution and suggests a Republic – which means breaking feudalism, of course, and dismantling the guilds, and rewiring the political philosophy of the Kingdom and he promises a small, hardly noticeable Revolution. Teeny.

The Paladin climbs out the window as the stabbing begins.

Hey, at least the murder hobos liquidated the dragon hoard into a Kingdom, power, land, and loyal ex-mercenary lords!

3. Find a new dragon

Maybe the murder hobos, playing these scenarios out in their head, realize the hoard is not worth it. There is such a thing as too much money. Instead, they go on a quest to find a new dragon, lure him back to the cave, get him to sit on the gold and, occasionally, very occasionally, terrorize the local peaceful peasant village. Having one village terrorized is a smaller evil than the entire collapse of the Kingdom, right? The Kingdom must persevere in the face of… them. Finding a new dragon is a good choice.

This could have been easy, though. It’s just too bad that, last week, the murder hobos capped Slim Jimmy and put Slim Jimmy’s Obviously Evil Dragon Raising and Breeding Ranch Emporium to the torch. Slim Jimmy was evil! He was evil breeding dragons. He was going to unleash them on the Kingdom! Or maybe he was selling them to murder hobos in sudden need of dragons to sit on hoards. In the fantasy universe, where there’s a business model there’s a business man.

If the murder hobos are lucky, Obviously Evils is a dragon raising chain across the Kingdom with outlets in all the Major Metropolitan Areas. But their price list – wow. High. Raising dragons to sit on hoards for adventuring parties is not cheap. Someone has to cover those feeding and muckraking costs. Even a small dragon costs almost a dragon hoard. The murder hobos will need cash to dispose of their cash. Surely there’s a slaughter-able Arch Lich or a Beholder Lord on their way out there, and that can’t possibly cause any problems…

A Conclusion of Sorts

There’s a fourth option, establish a bank, but that went to a whole dissertation on monetary exchange rants, debt financing for kings, and slowly purchasing the empire. Completely feasible but it ends in party stabbing. Someone has to be in charge. Also it was an entire blog post in itself – maybe next week. So let’s just say that ends with all but one member of the party dead, the last one a neutral evil paranoid, and an extensive crime family. So it’s the Rogue that wins that one. Good going evil!

In old D&D 1st Edition, at 10th level, player characters build their Stronghold as a sink for their filthy lucre. But that was an earlier, more innocent time when the game abstracted less of the real world. Clearly when the game ended the party members were Kings and Queens and Lords and Dukes and such and suchlike. A better time. An easier time. A time when TSR published splatbooks with monetary exchange rates.

The moral of the story: leave the dragon on his coins. Let him sleep. It’s better that way.

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His Majesty is interested only in wizards, alchemists, Cabalists and the like, sparing no expense to find all kinds of treasures, learn secrets and use scandalous ways of harming his enemies …He also has a whole library of magic books. He strives all the time to eliminate God completely so he may in future serve a different master …

– Propositions to the Archdukes in VIenna (1606)

“True it is,” the Court Alchemist says to the King, “without falsehood, certain, and most true. That which is above is like to that which is below, and that which is below is like to that which is above, to accomplish the miracles of the One Thing…”

“When will your laboratory provide me gold?” the King asks.

“Soon, my Great King,” says the Alchemist. “We are close to understanding the secrets of the Philosopher’s Stone. Simply a few more weeks of research and a few thousand more gold. It is delicate. One cannot rush enlightenment…”

The Great Alchemical Scams

Now since the principal part of our work consists in knowledge of our hermaphrodite, that is to say Mercury, guard well that you take it not for the leprous, common and vulgar mercury, in no wise proper to this subject. But where will you then – you ask – that I seek and find it? I answer that he is imprisoned and bound by many chains, and that there be none but the Philosopher can deliver him and set him free.

– Concerning the Material of the Stone, Anonymous

Alchemists claim Alchemy is the oldest science in the world with a theoretical history stretching into the mists of forgotten time. They say, by manipulating the elements, alchemy advocates inner awakening, enlightens the soul and grants greater insight into the universal magickal workings. These pseudo-scientists weave a tapestry of Hermetic Magic, mystical languages, astrology, numerology and chemistry to build an emotionally charged narrative opposing the traditional schools of magic with equally powerful effects. Why pay for a wizard when an alchemist does the same – and so much more! All their alternative magic needs is some seed money, a place to work, and a patron.

The Alchemists are running a con. The con uses three core scams separately or in combination:

– The Quest for the Philosopher’s Stone: The core quest for any Alchemist is the manufacture of the Philosopher’s Stone. The Holy Grail fusion of art and alchemical science, this physical substance could turn lead into gold or silver, prolong life indefinitely, act as a universal panacea, and be the very key to the riddles of the universe. The Philosopher’s Stone promised infinite riches and ultimate knowledge. Alchemists believed (or claimed) the search for the Philosopher’s Stone was an internal and external journey. Only the most pure find the Philosopher’s Stone. Its manifestation is the outward sign of complete hermetic enlightenment.

Outside of the Alchemist’s lab, actual wizards of the school of transmutation keep quiet about the Philosopher’s Stone. Sure, they know how to turn things into other things with magic but an ultra-powerful substance? What is this crazy talk. And no, they don’t know a thing about the overly successful but murdered Alchemist found dead in the street with no witnesses or the Alchemists turned to stone. Not a thing.

– The Elixir of Life: An immortality potion, the Elixir of Life is sometimes equated with a specific manifestation of the Philosopher’s Stone. Universally sought, stories tell of great Alchemists who drank “the white drops” (liquid gold) and achieved immortality without resorting to necromancy or eternal undeath. One only needs the slightest taste on the tongue of the Elixir of Life to extend mortal existence for hundreds to thousands of years.

Some Alchemists claim to have tasted the Elixir of Life and are already hundreds of years old – outliving the oldest of the Elves themselves. But there’s no proof.

– The Sovereign Remedy: The ultimate cure-all – not just for disease (easily supplied by Clerics) but for all ills and difficulties. The sovereign remedy is the solution to thorny political problems, the inability to see into the future, for old age, for infirmity, for mental illness and disease. It slices, it dices, it’s a salve, when applied, that will bring the dead back to life. The Sovereign Remedy is an infinitely refilling healing potion for no cost – curing all possible maladies, created in the laboratory with alchemical equipment, and made without Clerics or Gods. The Clerics warn these are scams but that doesn’t stop Kings and Emperors for buying fantasy cure alls with mountains of gold.

And so far, while the Alchemists write libraries full of Hermetic tracts and books on astrology, they have produced no real tangible results – that anyone acknowledges.

Why Do The Patrons Hire Alchemists?

Why would Emperors, Lords and Kings turn to Alchemists in a world full of wizards who cast actual fireballs and clerics who commune with real Gods out on the Planes? Why would these guys with advisors, education, money and power turn to alternative magi in their search for enlightenment?

– Wizards are expensive. Wizarding guilds set high and inflexible prices for their services. Sure a wizard potion will always do precisely what it says on the tin – wizards are proud of their workmanship and offer a high quality of product – but that potion costs 300gp. The Alchemist claims she can brew the same potion for only 100gp! Or cheaper! In a more attractive bottle!

– Wizards with any good reputation will not turn over their secrets to some Grand Duke for money. Some things are worth more than a bit of scratch; and while wizards love cash they won’t say, “Oh, the Philosopher’s Stone? I have it here in my pocket. Here, my Lord, take a bit! Gratis!” If a Lord wants to turn lead into gold and achieve immortality he’ll need to ask around.

Worse, some wizards are quite excited to part with their secrets for a steep price. The Necromancer happily offers his Lord the secrets of the universe and turn the Great and Magnificent Emperor into the Great and Magnificent Lich King Lord. Why, yes, he can Grant Eternal Life… wait, why is the King running away?

– The Lord cannot turn to scab wizards. Once a Lord hires a non-guild wizard, the wizarding guild blackballs the Lord for life. The Guilds have standards and they don’t need the Higher Classes. The first wizard guild rule is: customers only hire guild member wizards. Need to go to war? Need a phalanx of fireball throwers? Too bad you hired Bob the Scab on your quest for immortality. We cast him out for stealing our secrets and selling them on the street. Guess you’ll need to lose that war.

Wizards are petty like that.

– Wizards are loyal to other wizards. Their loyalty lies with their Order/University/Guild/Family. Even the sleaziest wizard’s absolute loyalty cannot be bought or bargained. Why would someone who can teleport and throw a fireball grant loyalty to a Lord whose best move is to call the Guard?

– A Lord can turn to the Church for magic and enlightenment… if the Lord wants entanglement in Church politics. Any Cleric will peer at the towers full of alembics and furnaces, the racks of dubious books, the magic circles drawn on the floor and the Neoplatonic sigils on the wall and ask probing questions. Questions like: what the hell are you doing? And, have you properly contributed to the Church this week? Clerics are serious hermetic buzz kill.

– Alchemists dazzle. They toil in huge laboratories of bubbling tubes and flaming furnaces with dozens – sometimes hundreds – of assistants. They speak and write in glorious, compelling code that tantalizes with a hint of higher truths. They make their Lords feel important. And Alchemists have impeccable fashion sense.

– Alchemists hook their Lord on the con. Their King is an enlightened Monarch who, with Alchemical Truths, leads his people into a great and golden future! Unlike the haughty closed-door wizards or the judgmental clerics, the Alchemist invites his great Patron along on a journey into philosophy, history, arcane knowledge, astrology, pseudo-mystical religion, and inner spiritual growth. It’s art! It’s magic! It’s the theater of the world!

It is, amortized over time, more expensive than paying a wizard.

Who Are the Alchemists (in a Fantasy Setting)?

The bulk of alchemists are straight up grifters and con-men – high charisma Rogues and a handful of Arcane Tricksters. To manage the con, they require fast talk, a glib mastery of alchemical terms, knowledge in handling alchemical tools to make small but impressive results (magnesium flash-bombs and the like), slight-of-hand and an excellent sense of fashion. They also need an underground contact to float them a supply of small gold nuggets to show “progress” in their “search for the Philosopher’s Stone.” These rogue alchemists are actual chemists – they can work a bench – but their expertise lies in true transmutation: turning words into gold.

These rogues have a standard modus operandi. They lay hands on a letter of invitation or hook themselves up with another Alchemist of solid reputation as an assistant and ingratiate themselves into a Court with high promises and theatrics. Then they ditch their Alchemist buddy, run a savage burn on their patron, publish a few pamphlets full of garbage, and make a big show of building a laboratory with tiny incremental results. They soak the Court for cash until their Patron gets exasperated. Then, just as the heat picks up, the Alchemist packs up his bags and wheels across town to run the same savage burn on the next Lord. With their freshly written pamphlets in hand and a growing reputation as an Internationally Renowned Alchemist, they can keep the con going for years. (See: history’s great charlatan, Edward Kelley.)

The second group of Alchemists are the real deal: the charismatic Sorcerers and Warlocks. Unable to become normal socially accepted wizards in the cities through standard means, hunted to near-extinction by the wizarding guilds as competition and scabs, these truly magickal Alchemists use the endless parade of con-men as their cover. Con-men to the Courts throw metaphysical flak into faces of would-be witch hunters while the Warlock and Sorcerer Alchemists use their (real) magic to keep their positions with the courts solid. Dressing well, impeccable manners and producing for their Lords, they hide behind the courtiers and their Kings.

These are the Alchemists of solid academic reputation: the real “magic” scientists. Unable to communicate in the carefully articulated language of wizard arcana but possessing high charisma and real magic, these Alchemists use the coded and hermetic language of alchemy to cover, and explain, their actual abilities. Like the con-man rogue, the Warlock and Sorcerer Alchemists are truly chemists and doctors – they perfect skills at the bench and in a laboratory in the service of their patron while writing books on their findings to further “the sciences.” The difference between them and the con-men: they get dangerously good results. They walk a fine line between con and discovery.

While the payoff is high, the Lord takes risk for keeping the Sorcerer and Warlock Alchemist on staff. The wild-magic Sorcerer may, randomly, explode the tower dedicated for alchemical research. And the Alchemist Warlock might slowly infect the heads of the entire Court with Cthulhu. But, who says the search for greater hermetic enlightenment is without a little peril? (See: Ramon Llull, Arnold of Villanova)

The final group of Alchemists are those who use alchemy to a different end: the Spy Bards. Espionage and Occultism: the perfect pairing. These alchemists can rattle off the language of alchemy with the best of the con-men. They have contributed to the greater body of alchemical knowledge as a carefully cultivated cover over many years. And they often come paired with one of the con-men grifter alchemists to help get ingratiated into a foreign Court – the bard as the front and the grifter as the “assistant.” While they can make flash-paper and palm a gold nugget or two, the spy bard’s expertise is in encryption, ciphers, codes, mis-direction and information gathering – useful in both espionage and alchemy.

Welcomed with open arms into the Courts all over the world for their celebrated knowledge, these bards talk their way into the closed boudoirs of the rich and famous. They use a little bit of alchemical fast-talk to make friends and cultivate moles. Then they are off sending back encrypted messages to their home Courts. Once the Lords are on to them – or bored with them when they don’t get results – the bard takes her leave and exits stage left, to head to the next Court down the road and do it all over again. (See: Dr. John Dee)

To Wrap This Up

Even in a world of insane market controls the free market will find a way. It’s cunning like that. Building high inaccessible walls around access to standard wizardly-magic creates a perfect opening for all sorts of con-men, grifters, proto-scientists, thinkers, and spies to waltz their way into the parlors of the rich and not-so-magicked. They take advantage of inaccessibility to magic – there, but never cheap – to give themselves an opening. If the money cannot flow into the pockets of the wizards it will flow elsewhere. Where the gate keepers build gates, the con-men build scams around the side and to the left and offer it all for cheap.

In fantasy, Alchemists make great backgrounds for player characters, NPCs in court, an entrance to stories about the Planes (what if all of this crazy talk is right?), a tension between wizards and non-wizards, spy stories, and ridiculous scene-chewing villains. Imagine for a moment the con-man grifter who now has two hundred assistants, a tower full of bombs, and is running all sorts of heinous murder plots from his protected position. Who needs an Arch Lich when one is dealing with a high level, high charisma gnomish Rogue and her legions of fanatical minions who hides in a tower full of glass and fire? Evil bomb-throwing alchemists! Fun times!

Note: none of these Alchemists presented here actually want to do science. That’s a variant – the actual scientist Alchemist. Or the hybrid based on Paracelsus: an effective surgeon and chemist who carried the Elixir of Life in the pommel of his broadsword. But there’s no science here. Just a series of rogues, their cons, and taking advantage of some well-meaning Great Emperors of Empire.

Writer’s Note: When I was writing this, I kept thinking the Bard-Rogue duo as the Mullet Espionage Team: business in the front, party in the back.

This is pretty short – I could write forever on Alchemical con men and rogues.

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Guilds are urban creatures. They cannot survive without cities. They are parasites on the fantasy body politic, reaching their spider-like legs into the deepest recesses of civic culture. Although membership is nominally voluntary everyone in town belongs to a guild: the doctors, the barbers, the bakers, the carters, the shoemakers and even the wizards. Especially the wizards.

Once enrolled one does not lightly leave.

The political powerful and wealthy Greater Guilds represent professions requiring rare and expensive educations. These powerful civic bodies wield true local power in their trade oriented Free Cities where the Masters of the Guild rule in tiny oligarchic republics without the meddling of Lords. Between them they divide and rule the Free Cities controlling war, conquest, trade, and industry. The Free Cities dance in their vice grip.

Within the Free Cities, the wealthiest of the Greater Guilds, Greater Divination Wizard Guild, is an autonomous moral and legal person. It possesses wealth in lands, houses, and money. It contracts, bargains, binds itself, and a proctor represents it in court. It built a vast University decorated with Coats-of-Arms. It has seals, banners and archives. It makes its own internal rules which supersede many local laws for its members and all members of associated, lower Guilds. Within the Free Cities’ jurisdiction, the Greater Divination Wizard Guild is self-governing. In a pyramid of city power, local lesser local craft guilds swear allegiance to the Greater Divination Wizard Guild for their own benefit and wealth: the wizard reagent reseller guild, the wizard jeweler’s guild, the wizard parchment makers guild who sell watermarked parchment for scrolls, and the wizard’s haberdasheries for highest qualities in wizarding robes and excellent wizarding hats.

Anyone with money, wealth or ambition schemes to join the guild and the easiest way is at the bottom: with apprenticeship.

A wIzard starts as a lowly guild apprentice. All entrants to guilds, greater or lower, mercantile or craft, world-spanning or local, starts with parents offering their precious children at age 10 to Masters on a contractual agreement. Some contracts result in cash, some in goods in kind, and some in promises around the care of the child. After signing, the child leaves home with precious few personal belongings and enters the world of the Master’s workshop where they learn a trade while doing the Master’s unending bidding. Some of the Masters of the Guild are kind, but most not; they have to uphold their reputation for turning children into wizards and only eight years for each child. Eight years are barely time to learn the basics of the wizard’s craft and not enough time for kindness. Long hours, constant work, uncomfortable conditions, and rote memorization is the norm. Wizard workshops are brutal places to matriculate.

Not all children have the magic spark. Some lack the talent and the mental agility. The weeding practice is merciless. Master Wizards trade children who fail to quickly display magic to Masters of the lesser craft guilds for anything: goods, money, servants, other apprentices. Society bars these failed children from the higher strata of their city’s class structure and doom them to a life of labor pressing paper in the wizard guild’s parchment mills or tailoring proper wizard cufflinks. Failure in the Master’s workshop means a life toiling in service to wizards, never quite belonging to them, knowing you could be one of them, but on the outside forever looking in. Once in as an apprentice to a Wizard Master – don’t fail.

Those who master enough “passable” cantrips may call themselves wizards and graduate from their Master’s workshop after eight years. On that day, these new wizards are full dues-paying members of their fraternity for life. While some newly minted journeyman wizards migrate to the next Free City over in search of work, few ever progress further in their mastery. Instead they find themselves in lifetime mediocre salaried service to their Greater Divination Wizard Guild in its voracious need for cheap and easy labor: writing detect magic and identify scrolls marked with the watermark of the guild for pay, tied to benches in magic item factories crafting for sale, or offering their clerical services cheaply to the city. Being a member of the vaunted Great Divination Wizard Guild does not guarantee success: many young wizards exiting the workshops of the Divination Masters find themselves bound for life to identify spell kiosks just outside popular dungeon and monster caves, identifying items and collecting data for unknown Guild Masters. If they just work harder…

But it’s good being a loyal guildsman. The journeymen who do choose to stay journeymen for life exercise a number of perks for membership in a wealthy, powerful guild. The guild is fraternity of educated men and women. It’s warm. It’s welcoming. For those who quietly toil for their brothers and sisters, the guild provides them with a salary, gives them access to lower craft guild services, throws them banquets on holidays, pays for Church help when they or any of their family are ill, buy rounds of drinks and bails them out of jail when they get into a drunken bar fight, shelters them if they are homeless, gives them a stipend when they are old and pays for their funeral at their end of life. Members can wear the coat of arms on their wizard robes. The Great Divination Wizard Guild provides. Sure, it takes a large cut of whatever the wizard makes but look what a member gets in return!

Most of these journeyman wizards never progress past First Level. But who would ever want to leave the city or the comfort of the guild?

The Guild Masters encourage those few young journeyman wizards with strong enterprising spirit to go out into the world. Leave the Free Cities. Band with murder-hobos. Discover mystery and excitement. Gain a few levels. “And bring us back what you learn,” say the Guild Masters. Pointy hat on head, staff in hand, shocking grasp cantrip in mind, the orks will take care of these optimistic few. Dead in caves, on dungeon floors, in wilderness, and on the bitter end of jagged rotten iron hobgoblin swords, the great yearning for adventure solves the Guild Masters’ future wizard problems. The few survivors are a more manageable long term problem.

The Masters can deal with five high level wizards. They have uses for the five high level wizards. The rest is what Bugbears are for.

Because the Guild Masters desire control and the status quo. They brook no challenged. The guild has internal laws and the members must obey the laws if they wish to continue reaping perks. Shops must not sell what the Masters say they cannot sell. Wizards must not scribe spells on non-guild approved parchment. Wizards must not wear non-guild approved robes. Wizards must not use competing guild’s magic items. They cannot learn or cast non-guild approved spells. No one in the Free Cities may hire a “foreign” wizard – and “foreign” has wide connotations. The Masters maintain a complete iron monopoly grip on their domain.

To maintain control, without any forewarning, the Guild Masters sends out bands of Searchers – the Guild’s own Black Internal Affairs Squad – to Wizard workshops, mills, and storefronts to ensure complete compliance with the laws of the guild. Discovering reagents purchased from non-guild storefronts and hats made by non-guild approved milliners is grounds for censure. Spellbooks found with non-guild-approved scrolls or, worse, scab scrolls results in Searchers confiscating the workshop and member banishment from the guild. The Searchers are on the spot judge, jury and executioner. There is no appeal. And the Guild Masters always know.

Fear in the name of inner harmony, city peace, and civic brotherhood togetherness. But why worry about the Searchers if the wizard has nothing to hide? We’re all brothers and sisters.

Some wizards banished from the guild flee the Free Cities guild jurisdictions to craft their own, new spells on their own pressed parchment. Spells the world has never seen. Spells that may, if popularized, change everyone’s life. The Guild Masters cannot abide rogue wizards and spells they do not control. They are inherently ultra-conservative; change cannot permeate the membrane of their carefully designed guild fabric. If someone outside mounted a charge to their authority, the Guild Masters could lose a small sliver of power.

The Masters send out teams of witch-hunters into the black swamps or desolate, forgotten wizard towers where the apostates hide. “Find these evil wizards and bring them to justice,” the Guild Masters implore adventurers (which include one of their own), “as they are destroying our way of life. Keep the magic items in those dungeons and towers you find. For greater glory! And bring us back the secret spell the evil wizard was working on, will you? Along with his head.”

The guild promise of progression from apprenticeship to journeyman to master is a lie. Theoretically, entrance to Mastery in the Wizards Guild is a meritocracy. Purchase a workshop from years of back-breaking labor and adventuring and accept apprentices. Take a place at the table of Masters. Enjoy the money and power. The old wizard earned it.

Wizards chase this carrot on a stick their entire lives. Work hard enough, pay enough dues, play the game, show enough unwavering loyalty, do the dirty work of the guild and be admitted to the higher ranks. Claw into middle-management.

Yet, the licenses for Mastery in any of the Wizarding Guilds are few and jealously guarded behind a web of examinations, payments, and complex secret mystical rituals. The Guild Masters goad potential would-be Masters to throw them another grand banquet, kill another guild apostate, and give another vast donation. The Masters promise to place the candidate’s name into the bag for possible election to the Masters when an Old Master dies. Pinky swear. And when an Old Master does die, the Guild Masters confers their one available master license to their own progeny to perpetuate hereditary line of families controlling the Guild. Bloodlines, they argue, are the best proof of future mastery over the difficult, higher-level Magickal Arts and the difficulties of navigating city politics. Who else to bring into the top ranks of Mastery than those who were born and raised into it? Fair? No. What is fair? Surely there’s another adventure to go on, another dragon to slay, another Plane to map, instead of getting dragged into the mundanity of politics of civil city life? This is a place for diplomats, not battle-hardened soldiers.

Hiding behind the Guild Masters of the Great Divination Wizard Guild, protected by this hereditary cult of Guild Masters, perpetuated by carefully cultivated nepotism, coils a layer of black secrets.

The Secret Masters of Divination are masters of information. They know all, see all, understand all. In times forgotten they built their guild on a core of wizard-based sensors armed with divination spells – information gatherers. They run the Searchers. They choose who to hunted and who to ignore. They declare wizards apostate who climb too high into their ranks. They sit on masses of data, sift through it and divine who to promote and who to destroy. Some whisper the Secret Masters of Divination are an Arch Lich, a Mind Flayer and a Beholder who steer the Great Diviniation Wizard Guild toward acts of unspeakable evil. Others claim the Secret Masters are seven 20th level gnome wizards bent on Gnomish World Domination.

In the bowels of the Free Cities, under the streets and deep in wealth-bedecked guildhalls, protected behind layers of mundane journeymen wizards and their legions of servants, the Secret Masters run a massive intelligence operation: a Black Chamber. Within, the Secret Masters filter all the information gleaned for their member’s spells, they read mail, they crack the most powerful codes, and they know all about Lords, the Kings, opposing Wizards, and Great Families. They run a world-spanning operation and sell their information only to the highest bidders when it suits their purposes. The entire guild operation – the city government, the greater guilds, the lesser guilds, the mills, the scrolls, the magic item factories, the workers, the apprenticeships – are designed to fund this massive, expensive secret operation. For whom? No one knows.

The Secret Masters employ special wizard agents in the Black Chamber to analyze the data and concoct new advanced ways to spy on the enemies of the Free Cities. They recruit from within the guild: promising journeymen wizards matriculating from the best Master’s workshops are “encouraged” to go on adventure and, if they live, come to work for the Secret Masters. Here, they perfect their Divination spells and ascend to the highest levels of wizard mastery. Beyond the control of the Guild Master front, these black agents move among their guild mates and perform the hands-on bidding of the Secret Masters – information collection, murder, mayhem, ant-spy deflection, whatever actions the data dictates. Outside the Black Chamber, these agents look just like another journeyman wizard.

Anyonemight be black agent of the Secret Masters. Anyone.

Or say those who can’t climb into the ranks of the Masters. Who knows? It’s probably all a crazy rumor. Guild membership and mastery might just be about temporal City-wide power, money, monopolies, trade, wars and control. Maybe the Guild Masters are a front for run of the mill every day evil. Funny thing about Masters of Divination – they are also masters of countering divination spells.

Writer’s Notes:

I had this idea in my head for the Diviners running a sort of horrible Medieval post-WWI intelligence agency – the forerunner of modern intelligence operations. The Divination spells in D&D5e strongly correlate to information collection, data mining, and sifting. Then I came across the “Cabinet noir.” And found other references to other Black Chambers, including the American Black Chamber.

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The party stands before the Duke and he gives them a charge: march up the mountain to a nearby kingdom and slay the Arch-Lich who lurks there. The Duke provides the party with maps to the mountain, a summary overview of what they might find (high level henchmen, nasty guards, a dragon chained in the basement) and offers useful magical equipment for the adventure. And God Speed, the Duke tells the party: the Kingdom and its people depend on you. Defeat the Arch-Lich and forever be written into the annals of history!

Off they go into the mists of tale. But this is not a story about the party heading off to grand heroics.

This is the story about the intrepid spies who stole the maps.

Even guards in evil kingdoms need to eat. It’s a funny thing about the bard driving the food cart. She spent her life learning to play all the roles for the stage and the role of her life is selling a bag of apples and a barrel of beer to an evil guard quartermaster in charge of feeding the rest of the evil underlings and cultists who surround the Arch Lich. She must build trust. She’s all about the confidence game – a natural-born grifter.

This is the core of a bard. Yes, the bard can sing songs to buff up a team and work support, but what the Knowledge Bard, a graduate of the Bardic College is good atare skills: the languages, the persuasion, the investigation, the perception, the stealth and the performance. She can carry out a role. She can track down a mystery. This knowledge-based bard is a master of languages. She has no communication barrier, not even with the evil races. She knows funny stories about everyone. She can sing a couple of songs. She is the master of selling roles to her audience of one and persuading them to trust her. She can run a con like no one’s business.

Outside in the courtyard of the Arch Lich’s compound, the bard and the evil quartermaster get along like lifelong friends. Next thing she knows, the quartermaster is inviting her in for tea. Then she bribes guards on the inside with treats. Evil guards are treat-deprived because they serve an evil Arch Lich and evil Arch Liches don’t go in for tiny sweet cakes. It’s not a sweet-positive atmosphere. Who is going to turn down a muffin? Are you that evil? Gratis, you know, between us. And don’t mind my two friends over there – they help to unload the cart.

Then, she has her team in. The bard schmoozes and builds up her network. She gets a few people to talk, and they introduce her to bigger people who will know more information. This is a long con. Be the role, sell the roll, and don’t get caught. After a while she’s one of them, part of the trusted inside. She’s always been there. She’s the one who brings the muffins. Getting caught means jeopardizing the job and blowing cover and possibly getting killed. Now she needs her team to steal information about the fortress and the Arch Lich’s plans.

This is a high risk, high reward sort of job.

The spy bard works her wits, her skills and her spells. While the bard spell list looks nearly unusable for standard dungeon-crawl murder-hobing, it’s fantastic for gathering human (or in-human) intelligence. She doesn’t have the big boom fireball or lightning bolts but her bardic spell list allows her to survive in the hostile environment beyond enemy lines where compromise is a constant risk.

The best of the best on the bard spell list:

Message – The ultimate spy cantrip, Message’s singular ability is its ability to travel through a ceiling to the next floor or around corners. It’s bounded by 120 feet (12 floors assuming 8 foot ceilings) or 3 feet of wood (about 6 floors, total, assuming joists). Working with a team, Message can get alerts – I’ve been nabbed! – through a building, a palace or a decent sized compound instantly.

Illusory Script– Essentially short term “cryptography by magic,” Illusory Script will encode one message that only decodes for the target. Highly useful for making copies of documents before they’re properly encrypted. This spell assumes the message will not pass through the hands of any creatures with True Seeing like, say, an Arch Lich, so use judiciously.

Unseen Servant – An easy way to perform a lengthy, repetitive task, like encrypting a message by hand; see below.

Magic Mouth – For passing along cryptographic keys, locations of dead drops, names of contacts and warnings, Magic Mouth is the perfect spell for communicating information between team members securely in a close and dangerous locale.

Non-Detection – Non-Detection is the diviner-busting spell. For 10 minutes, the target of non-detection can get through any magical scrying or divination defenses. The perfect spell for that high risk break-in, highly sensitive conversation or that Mission Impossible theft. Essential for pulling off a job.

Zone of Truth – Need to get absolutely accurate information out of a contact? The downside of Zone of Truth is the target knows they’re in a Zone of Truth. Using the spell will burn a contact, but if the information is critical to the safety of the Kingdom and all those innocent people…

Sending – More powerful than Message but less easily cast (as it is 3rd level), Sending gets 25 words anywhere, to anyone. 25 words is enough to transmit a key to a much longer bit of ciphertext to a receiver or reveal emergency information. 25 words is a tweet! It’s the SMS of spells.

Clairvoyance – Clairvoyance is an alarm system. For 10 minutes, the bard gets a sensor on a door that detects intrusion. That’s how long she has to meet with her network contact to get information, or commit a quick murder, or perform a little larceny. 10 minutes to get in and get out with a reliable watch.

Spells aren’t enough to infiltrate and share information about a high risk target. A good run against a target requires spells and skills – mostly involving data. Encrypting information by hand has a few strong advantages over the spell Illusory Script or a Sending: it is longer than 25 words, it lasts longer than 10 days, it cannot be detected by a Detect Magic, cannot disappear with Dispel and cannot be instantly broken by a creature with True Sight – which, well, Arch Lich. Or a high level Diviner in the Lich’s employ.

The bard is a cryptographer and an a cryptanalyst. The Linguist feat enables the bard to master most languages and cryptography is manipulating language to make it indecipherable with a secret key – or crack the enemy’s codes.

This is the essential tension between the game of intrigue and the spy bard. The spy bard’s network needs information to effectively deploy military resources and those being spied on must intercept and break codes to further their interests. It’s information and intelligence providing internal security and external offense against the enemy. Bards have the skills, the motives, and the creativity to keep one step ahead of the enemy’s current technology.

The stronger the key, the stronger the algorithm, the more unbreakable the code. The bard needs unbreakable codes – her life and the lives of others hang in the balance. As the spy bard lacks a computer (it’s fantasy), she has two classes of ciphers she can roll by hand at her disposal: alphabetic ciphers and one-time pads.

Alphabetic ciphers include the classes of substitution ciphers. The spy bard knows enemy bards on the other side who intercept her messages can trivially crack simple monoalphabetic ciphers with frequency analysis. She has to assume her messages can – and will – be intercepted by fate or by violence. If the enemy catches and deciphers her messages, the intelligence is lost and she’s probably one dead, or undead, spy bard. They can’t be deciphered.

She employs a whole bag of techniques that come with her Linguist feat to slow and befuddle her enemies and increase the difficulty of her ciphers: she can insert random characters, she can encode spaces and ‘nulls,’ she can encode syllables instead of single letters, she can use codes inside her encoded text, and she can layer the cracking process with nasty little traps. She can get very clever and use variations on the monoalphabetic cipher by using multiple alphabets to encode the message. If she has time or tools, she can even use the Vigenere Cipher, a nasty polyalphabetic cipher extremely difficult to break by hand without time and a good way to guess the key. Breakable, yes, but perhaps not before the spy bard and her team can get away.

The other option, and a favorite of spy bards, is one-time pads. One-time pads are virtually uncrackable without the key because they are completely random – the ciphertext gives no footholds in the sheer, icy cliffs of cryptography for enemy bards to crack with frequency analysis. It works like so:

The bard takes a highly sensitive message and one of her favorite plays or songs.

She works through the work of art and gives every word a number.

She replaces the letters of her message with numbers, each number corresponding to the first letter of a word in the work.

She delivers a big list of numbers on a page.

Using Sending or Magic Mouth, she drops a message about the work of art to her teammate or a bag man – in effect exchanging the key in 25 words or less at a time delay.

No Diviner, no enemy secret agent, and no magic spell will crack that code if it’s intercepted. However, this technique has two major weaknesses:

The bard somehow give the key to the intended target of the ciphertext. If she cannot cast spells, or is not high enough level to use messaging spells, she will need to rely on a back channel.

This work can never be used in another one-time pad so the bard needs a nearly inexhaustible supply of plays and songs. Luckily, she is still a bard.

As a quick bard hack — Cryptography is a labor-intensive and slow process by hand unless one has unseen servant. Much of the task of enciphering and deciphering is rote – look up the chart, look up the key, look up the ciphertext, write the ciphertext down. Repeat. Unseen Servant is a short duration programmable spell which performs a task a human servant can do – like writing down letters or looking up charts. As difficult as it is, the bard can automate much of the labor for efficient communication and gain critical minutes using magic.

The bard cannot pull off the entire savage burn on the evil Arch Lich without an infiltration team. She’s a fantastic cryptographer, she speaks all the languages of evil, she can make friends with the Arch Lich’s closest henchmen and get them to spill their plans. But she cannot get into the Arch Lich’s inner sanctum to steal the Lich’s phylactery alone. She cannot get herself out if she gets into a fight. She’s a Grifter. She needs an Infiltrator. She needs a Hitter. She needs her crew.

The Infiltrator is a Trickster Rogue. Fast and intelligent, the trickster rogue is a master of the three finger discount. The bard is the face of the operation; the trickster rogue is the action. Her job is to break into bedrooms and steal plans, hide in ducts to overhear conversations, sneak into the dungeons to release high value prisoners, execute a couple of targets with backstab (and True Strike), get in, get out, and get away with the maps in her underwear. She employs a subset of the Bard’s spy spell list – she has Message to keep in contact with her party members – “Guard patrol on level 5,”- Disguise Self to meld in with the guards or the servants, a little Charm Person (“These are not the orks you are looking for,”) and, when detected, Sleep. The Infiltrator uses Illusory Script as the microfilm camera of spells to copy plans and leave the originals behind.

The Hitter is an Eldritch Knight. A retrieval expert, her job is to protect the Bard and the Rogue when they get themselves into trouble. She’s not a hired killer, but she will kill to get her teammates out of a rough situation. Having enough social skills to pass as almost anything, the Eldritch Knight can double up as a Grifter to back up the Spy Bard. Her Mage Armor and Eldritch Sword means never having to carry weapons into a possible combat zone – she has them when she needs them. One the job goes bad, the Infiltrator is on the run and the Spy Bard is talking her way out of being hung from the nearest rafter, the Hitter can reach out for her sword and start going to town. Hope the Bard has encrypted all the documents sufficiently when they get spotted while running away…

The three methodically plan out their the savage burn on the Arch Lich because that guy has to go down. He’s bad news. The bard provides a cover for the team (“I’m a bard and these are my roadies!”), builds up her network of contacts, works a the human side of the intelligence chain, defeats the diviners the Arch Lich may have on his staff, and encrypts the data to smuggle out. The thief lifts the plans about the Arch Lich’s army, his dragon in the basement, his phylactery, and makes off with the Arch Lich’s inexplicable pair of Boots of Striding and Springing. The thief also performs a little covert ork and hobgoblin murder. The Eldritch Knight smacks people in the face when it all goes bad because it always all goes bad. Getting out is difficult; sometimes she stabs some former ‘friends.’

They are a highly trained team. They work on hire. They answer to no master – that anyone publicly knows about. They coordinate on a job through well-placed Message, Sending, Magic Mouth, dead drops, and signals. The job is to get in and get out. Preferably without getting caught or setting the Arch Lich’s castle on fire.

When a Kingdom needs help to deliver them from evil, these are who they call first.

In this particular example, we can assume the run went smoothly. The bard talked the team in under the nose of the Arch Lich and made some friends. The team set up dead drops in secure locations inside the Arch Lich’s compound. The thief bloodily murdered a few orks with death from above. The team discovered the Arch Lich’s horrible plan. They snuck out by cart — “You’re out of beer!” – in the night. The Eldritch Knight cleared out patrols on the way home. They smuggled their encrypted information to the Duke, who handed it to his cipher secretary for decryption.

Then the Duke called in the main hitters, the fireball wielders, the combat team and handed them the decrypted intelligence. Here you go, a ready-made adventure for heroes to go roll an Arch Lich for the good of us all…

Pre-Build Team:

The focus was mostly on the bard but the bard needs a posse. To express the complex idea of how to build an infiltration team and how the spy bard works in practice, we put together some example characters. This pre-built 5th level infiltration team is a group of highly trained women operatives and mostly ready for play. I didn’t write these – all credit for these character sheets goes to my research assistant (and husband!) by Eric Thornber.

Writer’s Note: This started as a discussion on twitter about D&D/Shadowrun cross-over. This is less socio-economics and more world-building but gets at a long standing issue: the Bard – what good is she good for? It turns out in D&D5e, she’s the lynchpin in a slightly different class of stories than the standard smash-and-grab murder hoboing. Then I really enjoyed the idea. Unfortunately, I ran out of words, so I may continue into a major Crypto Bard vs Diviner Underground War write-up next week. This is less intrigue than I would have liked.

The team at the latter half of the article is based on Leverage’s Hitter/Grifter/Hacker/Thief combo with the Bard filling the role of the Grifter and the Hacker. The Bard and Rogue are essential. The Hitter can be swapped out for a Warlock and a Sorcerer, but the Eldritch Knight was the most fun.

While writing this I came across the Chevalier d’Eon, the best example history could give me of a transgender spy bard because awesomeness.

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A bard dashes through the back rooms of a palace with secret plans in his hands. The guards are after him. The bards desires escape and the best way to slow the guards down is to throw Arcane Lock on this door and then go out the window. It requires 25gp of gold dust. With sweaty palms and heart thumping in his chest, and mere moments to go, the bard is not going to whip out Mordenkainen’s Guide to Commodity Prices Across the Realms for the current week (picked up wherever good books are sold!), flip to the G section for gold dust and look up the current market trade price of this baggy of dust in his hand to ensure the commodity market for gold has not significantly shifted since he entered this palace and got it on with the Duke’s daughter. “Wait guys,” the bard could say to the guards, “Before we can do this, I need to check my actuary tables.”

But prices do change based on a whole host of conditions – sometimes very fast. So we ask: without any market information, how does the spell know the gold dust was worth 25gp?

I offer three possibilities:

Quick Sidebar: Tracking reagents by price instead of weight is a flaw in the game system. For example, continuous flame requires “25gp of ruby dust, consumed on casting.” How much ruby dust does 25gp? 1oz? 8oz? 1000lbs? If the local economy prices 25gp at 1000lbs of ruby dust, no one is casting continuous flame. “Just back up the dump truck here, George,” the wizard says. “I need to light this here torch. CONTINUOUSLY.” After doing some quick calculations and looking up turn of the 20th century actuarial tables in Google Books and did a hand wave to allow $10 ~= 1gp, it takes 125lbs of patchouli to cast Legend Lore.

We roll with this idea and its implications for fun.

#1 Least Interesting: Delusional Belief and Fiat Reagents

The spell-caster, who purchased a small diamond for a magic focus for chromatic orb for 50gp from a trusted jeweler, believes the diamond he uses for his spell is worth at least 50gp. The wizard is confident in the price he paid for the diamond. He casts chromatic orb. His target takes 3D8 damage.

Maybe the diamond is actually worth 50gp. Maybe it’s not. Maybe the diamond is really a chip of elaborate glass sold by the Thieves’ guild and the wizard only needs to believe the focus is worth 50gp. The unshakable belief in the original financial transaction powers reagent focus for the spell. The wizard better keep his receipts.

Spell reagent effectiveness based on belief drives a perverse incentive for the Wizard Schools, especially the School of Evocation, to ensure all sellers of small diamonds sold for chromatic orb price them at a floor of 50gp regardless if a free market would also price the diamond at 50gp. The Jewelers Guild must act as an “authority” on gem commodities, and through pressure and persuasion, the Jewelers price accordingly.

Wizards are not experts in rare gems. They’re experts in spells. They buy their focii from a “trusted seller” from the Jeweler’s Guild. The trusted seller assures the wizard of the reagent’s price, despite the price being arbitrary, and performs the financial transaction. Later, magic works. Yay!

Fixing the price of the small diamond suitable for chromatic orb at a floor of 50gp goes into a weird economic rathole of fiat reagents. A large, financially solvent entity, the School of Evocation, through “persuasion” implicitly backs any small diamond of suitable chromatic orb focus size at 50gp. It’s safe. It’s tradable. Anyone can carry 50gp reagent-grade diamonds and exchange them for goods and services worth 50gp. If Joe the Baker does not want to carry 50gp from making a large bread sale because it is heavy and obvious and a target for thieves, he can, instead, buy a chromatic orb reagent. Then Joe can pass it on to George the Weaponsmith for a 50gp-worth sword. And George can pass the diamond on again – giving the diamond a little velocity – to the taxman for his 50gp bill. No one needs to carry 50gp any more – not adventures, not anyone. Instead they can trade in “orbos” – chromatic orb spells – and price everything in the very spells which needed fixed pricing. Now the school of evocation isn’t merely a fixer – they’re a central bank.

Markets are nothing but a big confidence game.

This ends where Schools of Magic turn into National Banks issuing reagents as currency, builds the International Wizarding Fund and the World Wizarding Bank and give up chromatic orbing bugbears entirely because it’s more lucrative to run a global economy.

But this is all boring so we will look at possibility #2.

#2 More Interesting: Gods

This is simple for faith-based casters: A cleric holds up his diamond and goes hey, God, will you take this in exchange for resurrecting my buddy? And the God says, wellllllll you put in 5000gp of effort and time and it’s a super nice diamond so sure. Here you go. Resurrect away. Done.

But what about arcane spells? They don’t go whizzing off to some designated God for a price check on Aisle 9. The wizard casting chromatic orb might be a stone cold atheist.

Or do they?

Hidden in the Gray Waste there is a God who checks out arcane reagent pricing during spellcasting. And this God’s name is Mike.

From what little is written about Mike from the Planewalkers who penetrated his Palace, his avatar manifests as a paunchy, 50-ish balding man with a striped knitted sweater, oversized glasses and a paunch. This dour God-powered economist sits on his comfy chair surrounded by hoards of slobbering Yugoloths who wear green visors and counts piles of money and argue about externalities and incentives. They make anyone who broaches the inner sanctum do math… for eternity.

Mike is not a God of Trade. Mike is the God of the Market. He has a condo in Bytopia but mostly he dwells in Hades.

Long ago, when the worlds were young and enterprising experimental wizards discovered the spells and bound casting to focii and burnable reagents, Mike snuck in. With the help from his clerics, Mike managed to get tiny prayers built into the ritual words for vocalized casting. Wizards buy these reagents, right? Reagent pricing ping off Mike and he responds with a confirmation. That way Mike could ensure reagent pricing was fair and equitable. Just all part of his sphere of influence.

The worlds didn’t turn out the way Mike envisioned. He became small. The Realms, locked up as they are with guilds and Wizard schools and monopolies and lords and feudalism, culturally resist his sphere. Unleashed free markets would overturn order. Bring the mighty low and raise the low up. Destroy the status quo. Start wars. Bring the revolution and lay waste to entire kingdoms. Invent the joint-stock corporation. Pollution. Mass consumption. Corruption. A new order. Powerful human and God incentives keeps Mike where he is: small, glowering, and surrounded by actuarial Yugoloths.

Mike schemes.

Like any God, Mike has his cults. Few and worshipped only in the darkest places of accountancy back rooms. Mike directs his clerics to pry their way into the minds of the enterprising and seeds the plans to break down resistance to loaning money at interest. His paladins, armed with an oath of vengeance, track monopolist guildhalls – good, evil, indifferent – and burn them to the ground in the name of freedom. His cults back the secret underground black markets, the cottager networks, the rogue print shops, and anyone who dares to trade outside of Guild control.

But good to his word from when the worlds were new, Mike still performs a price check on reagent pricing whenever it comes to him through arcane whispers and verbal ritual. Every once in a while he fails a check because prices have drifted too egregiously or what the spellcaster uses as a reagent substitution is silly and the spell explodes in the spellcaster’s face. “Wild magic surge,” they say. Or maybe Mike.

But maybe it’s not Mike or any God at all. Maybe it’s…

#3 Most Interesting: Modrons!

Imagine this:

Some describe an economy as a giant super computer with people and goods as their programs and subroutines to generate pricing and commodity information;

A fair percentage of spells across all spheres of magic have a material component with a fixed cost needing verification;

Spells with fixed cost also have verbal components;

When a spell-caster casts a spell with her focus, the verbal portion of the ritual transforms into an arcane network protocol which flies across the planes and terminates at Mechanus;

A Modron picks up the ritual like an inter-planar REST call and processes it;

The Modrons in concert check the price against their infinitely running algorithms and return a YES or NO;

See, Modrons simulate everything in the planes in their giant Modron-based computation matrices within Mechanus. Modron economics algorithms are perfect and predict price fluctuations of all possible goods and commodities with startling accuracy given a starting point. Sadly, humans and other humanoid beings are not so predictable. Humans have an annoying habit of getting into wars, conquering each other, crashing their economies by basing them on chromatic orb spells, and other economic mayhem. And while the Modron algorithms are without fault the data is often not; after a while the results begin to drift.

Every Great Cycle or 289 years, to recalibrate their systems with a fresh data set, the Modrons erupt from Mechanus in a great horde and walk the Planes – in the Great Modron Marketing Survey. Modrons stop, buy, sniff, observe, and utterly destroy whatever they pass through. They collect data about all the commodities on the Planes and build elaborate tables – which carefully promote to the highest level Modrons on the Marketing Survey for safety and CRC-32 data validation. It may look like Modrons are burning down your peaceful peasant village but all they want is the current price of eggs.

While few low-level Modrons survive the march – Modrons often catch a bad case of adventurer – the high level remainders straggle home and feed the freshly collected data into the rest of the great computation matrix of Mechanus via Primus. They restart the machine and off it goes.

Once the data gets into the system, the spell-to-reagent prices are fixed. A 25gp diamond for a chromatic orb is so big with such weight. However, every 289 years, give or take a few years, as the data ages the prices drift. Modron checks no longer reflect the correct prices of spell reagents. The percentage of spell failure slowly climbs. Then the Modrons march again and prices reset. Again, as the spells ping their little mystic-networked and highly distributed checks off Mechanus, they cast again.

A simple, clean explanation. With Planes wide destruction.

Bonus Content: A Heist to Run a Savage Burn on the Entire Universe

Someone discovered the truth of the Great Modron March and, through a series of events, has hired the adventurers. They have a plan but they cannot execute it themselves. The sponsor is old and likely frail and enormously powerful cleric. They need a group of high powered adventurers who are willing to take great risks for enormous financial rewards. They need adventurers to run a complex heist.

Here’s the thing: while the Modrons march, the Modrons freeze their pricing algorithms. But as the Modrons return to Mechanus and right before the few stragglers report to Primus, they reboot the entire computational matrix. At that precise moment, the matrix is open to a little data hijacking. Yes, someone, at great length and great pain, has discovered a hackable timing vulnerability in Mechanus via the Great Modron March. To make everyone richer than anyone else ever, all the party has to do… really just this… is to:

Pick a spell and its spell reagents;

Follow the Modrons on the last leg of the Great Modron March;

Sneak into Mechanus without being seen – clearly easy for adventurers of such great skill;

Kidnap a survivor from the great Modron March who, through the promotion scheme of the Modrons, is likely to be a high-ranking Modron;

Feed it the wrong information about said commodity;

Let the Modron go without being spotted so it uploads its bad data to Primus;

Go home and buy and/or sell like mad.

Any spells, magic, or economic data which relies on the Mechanus computation matrix will be wrong; every arcane spell-caster must adjust to a new value or have a critical spell fail until the Great Modron March begins again and resets. If the adventurers and their backers are prepared, they’ll clean up and make more money than anyone else on the Planes – more money than imaginable.

A few small catches, though:

It’s not easy to sneak into Mechanus without being observed because it’s Modrons and they are all hey look people in Mechanus this is data must share so this will need an Oceans-11 like plan;

High level Modrons put up a hell of a fight;

Feeding information into a Modron is a little bit of an ‘undefined requirement’;

And the Modron has to be returned to the end of the march without being missed.

The payoff… the payoff is enormous… and it will run a savage burn on all the wizards in the universe.

But who gave out the truth of the Great Modron March and the timing vulnerability? Deep, in the depths of the Great Waste, a forgotten God named Mike taps copies of a perfectly serviceable heist plan.

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This article assumes that 1st level identify spells are used in identifying and validating a large range of magical items whenever a magic item changes hands. For example, when an item comes out of a dungeon, when taken off an enemy after a battle, when validating an item’s nature, during a financial transaction, or with death and wills and the pearl is consumed in the spell.

Components: V, S, M (a pearl worth at least100 gp and an owl feather)

– D&D 5th Edition Players Handbook, page 252

Seldom do the clam divers find wild pearls. Only one in a thousand divers slices open a clam and finds a perfect white glittering orb inside. Pearls are a misfired immunization response to possible invaders within the clam shell – a round orb of calcites working as white blood cells to entrap a speck of dirt. A quirk of evolution which, before the Divination School of Magic, was simply a pleasant happenstance which neither worked for nor against the clam’s continued ability to reproduce and exist. The wealthy craved pearls for their extreme rarity. A string of wild pearls was worth a million gold. And then, pearls became a core part of the magic item economy.

The Divination School of Magic set up local Identify shops in every major town, city-state and trade cross-roads in the world. They work like any medieval guild: they enforce a certain level of service quality among their members, police services members can sell, and drive the right to who can and cannot set up shop. They maintain monopolies in their territory. And, like any other guild, they also offer members a carrot on a stick – the possibility the most diligent, most hardworking, and best diviners entrance into higher levels of Divination Mysteries. With entrance comes training in higher level divination wizarding spells. The Grandmasters of the Divination School of Magic are the best Diviners in the world – and rightly so because they have mastery over the spell Foresight.

Diviners in the local shops are 1st level Wizards trained in basic low level divination spells and cantrips. They dream of notice by the higher ups in their Guild so they can abandon their storefronts and go into actual wizarding. To do that, they must show a little entrepreneurial spirit and set up their kiosks where they will cast a high rate of identify spells per week. Every town with a major Adventurer or Magic Item presence has an Identify Kiosk. The Diviner needs a constant source of pearls worth at least 100 gp to service his clientele.

It’s unreasonable to expect Adventurers will supply pearls but perfectly reasonable to assume Adventurers will supply at least 100 gp. The Diviner buys pearls in bulk from a supplier and burns them in his spell-casting. We’ll get back to the Identify Kiosk in a few paragraphs but walk way with the scene of a Diviner at level 1 casting identify on a sword unearthed from a nearby ruin.

The Supplier of pearls is a merchant’s guild broker from one of two mercantile sea-side city states at war. The city states are at war over pearls.

Originally, pearls were rare things the merchants found in distant bazaars and sent to their home cities with big batches of black pepper, rare textiles, and spices. Merchants used these rare pearls to sell to or bribe the nobility. Once the Diviner’s School of Magic started buying pearls in bulk, the traders had classic supply and demand on their hands. They could sell the one rare pearl for an extraordinarily high price or they could feed the aggregate demand – but they needed to keep prices high, since pearls must possess worth at least 100 gp. The race was on, Lawrence of Arabia-style, to find enough pearl farmers so the merchant’s guilds could have fun with aggregate pearl pricing, and selling pearls in the pricing band. Things got twitchy once they located pearl farmers and supply lines stood up.

Pearl farming is a slow and dangerous business. Farmers seed clams and then harvest them underwater. Then farmers must wait an entire year before the pearls are harvestable. Beds are only good for 2-7 years and then beds rotate. Worse, it’s trivial for a clam diver to get swept up in currents and drown. Magic helps but clam farmers must expect casualties every season and magic is quite expensive. Unless one mitigates all those expenses. Brutally.

A sudden deluge of purchase requests from traders where there were none before incentivizes the clam farmers to produce pearls at an extraordinarily high rate and with a crushingly low overhead to maximize their profits. They require large clam farms, dangerous work, large workforces, and a quick replacement policy for those who die on the job. Merfolk are cheap, work underwater, are kept in cages, and fed chum. Remember all those low level adventures with fighting slavers? Why were slavers enslaving people? Pearl farming on an industrial scale to feed the voracious appetites of mercantile city states who have found a customer. And don’t forget the occasional enslaved wizard. Need to cast those spells to allow Management to breathe underwater and cast the occasional identify to check batch quality. That guy is on an adventure of his own.

Two city-states in close physical proximity selling pearls have a rent problem. The rent problem is simple: there are two of them.

Profits magnitude is not by who makes the most money overall but who makes more than the other guy. Say, for example, City State A and City State B both use the same slaver pearl farmers to get their supply and the pearl quality is roughly equal. Since they both provide the same service, and they both have their own merchant guilds selling pearls wholesale to diviners, they will both make equal profits. Sure, they backstab and murder while competing over groups of diviners and exclusive contracts but aggregated overall, both city states make the same money. If, suddenly, City State A reduces City State B to a smoking ruin via giant fireballs and could no longer offer the same service, City State A could offer better service for the same price and sell into City State B’s customer base. City State A’s profits would be magnified by how much City State B loses. And then City State A could start extracting monopoly rents from the Diviner School of Magic to raise pearl prices to exorbitant heights because where are you going to buy pearls? City State B? Why, they’re a ruin!

In infinite worlds, surely one exists where the two city states work out territories peacefully. Happily. They shake hands. Everyone hugs. In the other infinity-1 worlds, both cities hire a bunch of mercenaries, load some fireballs into trebuchets, and go to town.

History provides many means to enforce a monopoly but the most popular is violence.

And now, the pirates and black market. The Diviner’s School of Magic prefers a complete monopoly on the casting of identify spells. It is, after all, a divination spell and they are duly authorized to provide divinations. With enough money bribed to nobility and local magistrates, pearl supply and the casting of licensed and regulated identify spells are the sole province of properly licensed diviners. Any old wizard casting a divination is unlicensed and perhaps illegal. We don’t want wrong information about magic items getting passed around, do we?

Claiming the illegality of a 1st level and highly common wizard spell considering the political pull of high level wizards is a bit unreasonable. But it is not unreasonable to outlaw the handling of pearls without proper license. Black markets spring up when people desire certain substance but it is highly controlled or outlawed. The market, here, are non-Divination School of Magic wizards with adventuring groups. The supply comes from hijacking and theft – piracy.

Since pearl farming needs specific species of clams, the pearl farmer plantations operate overseas in exotic lands. When a batch is ready for market, farmers load pearls onto large shipping boats and the pearls head for trading mercantile hubs. Pirates hunt cargo cogs in well known shipping lanes, board ships, steal pearls, kidnap high value hostages, and sink the boats to the bottom of the sea. Piracy is incredibly expensive for City State A and City State B (although it helps keep pearl prices high – maybe they create their own buccaneers). “Good” City States hire adventuring groups to protect boats with cargo from pirates who are terrorizing the high seas… who then, after a thrilling adventure, take gear off pirates and get it identified. Adventuring is a long tail.

Unlike setting up a supply chain from farmers, locking in contracts with downstream buyers, warehousing, transportation and distribution, the black market has a relatively low barrier to entry. One pirate ship, one set of deals in a bar, and one big score of profits. Until one Thieves Guild grows dominant over the other smaller players and decides to grow into a full on underground economy. That entity enforces its monopoly through obscene back-alley violence. (Again, monopolies, violence.) Once one is already breaking a number of laws, it’s not a jump to just keep on going with the law breaking.

But it’s there, the black market, with all its backstabbing and murder. Thief gangs muscle into each other’s pearl selling territory, fight among themselves, and generally kill each other for their kingpins. And a wizard shows up at a grimy corner in a back alley slum and deal with skeezy thieves to get a baggy of pearls priced at exactly 100gp each so she can identify the party’s equipment from the last dungeon run. Maybe the baggy has pearls. Maybe the baggy has marbles. Maybe the baggy is full of pearls worth less than 100gps. The wizard takes a gamble with the thieves guild. Or the party can go to a fully licensed Identify Kiosk.

The wizard making back alley deals may get herself in real trouble with the Diviner’s School of Magic if she operates on enough scale. How would the Diviner’s School of Magic know unlicensed black market pearls and rogue identify spells? Well, hell, they’re diviners. And speaking of…

Let’s get back to our friend, the diviner, from way in the beginning. He bought his pearls legally from a merchant who has marked the pearls up and put on a ‘crossing a war zone’ premium on the supply. If the two cities ever flood the market with pearls, the pearls will drop in worth to under 100gp and become useless for identify spells* so the war and markup are good for business. It is in the interest of the Divination School of Magic to keep City State A and City State B at war and to destroy the black market to force price controls over their identify spells to ensure they work and to maximize their profits. Being the reliable source for identify is the kiosk selling point. It always works.

The Diviner’s School of Magic is not particularly interested in profits. Sure, profits help to fund their grand enterprise but they are not motivated purely by extracting rents from adventurers, militaries, magic item resellers, hordes of hobgoblins, or anyone needing a check on a magic item. What they crave is information, and what everyone hands over willfully in their transactions with the diviners is all the information about the magic items in their possession. It only takes a question to also extract identities.

This is the hook for the 1st level diviners: the more identify spells they cast, the more information they gather about the magic items in circulation – where they come from, who has them, what they have, where they’ve moved to. The more knowledge diviners feed back into their guild, the likelier they are “promoted” to a “higher level of secrets”and get out of the daily drudgery of casting identify spells. Low level diviners are knowledge forwarders to a centralized knowledge repository held by the Diviner School of Magic. The mysterious and unknowable Grandmasters know everything about everyone – who is adventuring, who is successful, who has what high level weapon or tasty piece of armor, what great weapon has fallen into which military’s hands. They know about magic item transactions between parties. They are a lovely secret society and highly integrated intelligence network for hire spidering their way across the realms – intelligence useful to both sides in a war. Would you like to know what magic items the other side has in reserve and how to counter them?

Why bother casting spells to look omnipotent when one can merely consult the hordes of accountants in the back room? Money is money but intelligence is priceless. Who questions the least of all Schools of Magic? Look at the evokers, they have fireballs! We merely cast spells to gain little bits of knowledge…

From Secret Grandmaster Diviner to a corner kiosk to a Great War to black markets to pirates and slavery and back to the adventuring party again with their fresh levels and unidentified gear. The arc of the supply and demand line from farmer to consumer is relentlessly neutral evil. Lost in this entire discussion is the forgotten cage of owls, somewhere, cold, forgotten, and completely bereft of feathers.

This brings up a whole different question of how does the pearl know it is worth less than 100gp that is on the topic list for later.

Writer’s Note:

The original conception for this idea was a knowledge problem. The diviners who identified magic equipment for 100gp always had the upper hand over adventurers because while the adventurers would know what magic items they had, the diviners would know the magic items all adventurers had since they identified them. It’s a small hop to incentivize sharing information with a secret cabal in a giant information network in return for cheap benefits ie, 2nd level. Then came trying to figure out how many identify spells needed to be cast/week to support adventurer groups, magic item transactions, death and wills, auction houses, etc and since identify is the de facto validation check much like an appraisal, the answer turns out to be “a non trivial sum.” It’s millions of gp in pearls/year with pearls at 100gp. And pearls are intensely difficult to come by from nature so that needs puts pressures all over society.

I am a big fan of the Diviner School of Magic as massive secret society/intelligence network and put together a few notes on why one would never use their services (ie, you’re the thieves guild/magic user underground). Also working on ways to counter them. This is a nice campaign idea to start from the slavers and work up through levels like an onion to the horrible reveal of the secret society apparatus about to be used for something horrible and that Grandmaster Diviner your wizard just learned from wants to eat the party’s face.

I also like cities at war because it’s a lovely excuse for high seas adventure: two maritime cities giving groups buccaneer’s papers to operate as pirates on the high seas for a ‘good cause’ by rolling each other’s ships. One can roll slaver ships and rescue wizards who maybe were sold into slavery by defying the Diviner’s Guild in the first place…

This is really the first cluster of ideas I would flesh out into something bigger with more meat. It really needs the 10K word treatment to work.

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The party stands on a beach on the other side of the world facing down an army of 30,000 heavily armed but lightly armored orks. And they wonder… how did we get here?

King Stephan II is at war with his neighbor. He no longer remembers what the war was about or how it started. It began in his father’s father’s time. All King Stephen II knows is war is expensive and the Royal Treasure is heavily in debt to a number of incredibly dubious concerns. He’s not worried about the debt, though. King Stephen II is phenomenally concerned about a more pernicious virus working its way through his Kingdom: boredom.

When war is good it’s very good. The realm has no professional standing army. Instead, when it’s time to go to war, the King bribes his Dukes to mobilize their private armies. The Dukes bribe their Barons, the Barons bribe their Knights, and the Knights rape and pillage the land to raise money for armor, weapons and horses which flows back to the Faires where the brokers make their cash.

The military is a loose confederation of adventuring groups, mercenaries, Knights and their buddies looking to grab a well-paying hostage, Barons trying to get ahead, and Dukes eyeing the Throne. Theoretically, all these groups show up at the same place at the same time after a fun trip through the countryside where they force local peasantry to fete their betters with enormous and locally expensive feasts. If all goes well, they route the enemy. The victors grab as many hostages as they can reach, and the Knights go on a rampage burning down the local villages. Everyone makes out well and the local treasury overflows with its cut from this heroic misanthropy.

The enemy has been busy with their own internal problems leaving King Stephen II with a multi-pronged problem:

Bored nobility.

His treasury holds dust and his creditors are circling.

The Good and Wise King can debase the coinage – he’s done this a few dozen times before – to raise more money for his treasury and squeeze the peasantry as the harvest is good. But his real problem is the nobility. King Stephen II is Half-Elven by some tangential definition of “Half Elven” – he claims an ancient ancestor was an elf and he possesses some great and noble elven blood. So do almost all of his nobility, even the Duke of Shoral, even though that Great and Wise Duke is clearly a half ork. (The Duke of Shoral claims not only an ancient ancestry of elven blood, he claims his half-orkness is a special expression of that blood.) King Stephan II is in truth only a man and he needs his nobility entertained otherwise they will begin to entertain themselves with each other. Nothing is worse than bored heavily armed personal militaries.

Wizards, or at least their agents, live on the Trade Nexuses. The Glorious and Most Serene Republic of Bavoria is just such a trade nexus. Built on the ruins of an ancient harbor left by the previous civilization who had excellent taste in city locations, Bavoria benefits from a wide, protected harbor, access to timber in the nearby foothills of the mountains, and excellent roads. In the far-flung past, Bavoria mostly did trade in honey, wax, and wine. Now it trades everything its network of brokers can buy from all over the world. With trade comes money, and with money comes the academic trades – the writers, the poets, the painters, the sculptors, the philosophers, the alchemists, the libraries and the universities. With the universities and an access to expensive and rare reagents come the Wizards. And the banks.

The Doge of Bavoria is a Transmuter and sits at the head of the Colainni family, an ancient family who were among those who built Bavoria in the mists of history. The Colainni family was a proud family exclusively of wizards but today most of the family business is in finance and murder – much more lucrative than wizard’s robes and runes. And the hats? Oh, the amazing hats. The Colainni family has managed to fuse the Merchant’s Guild with the Thieves Guild and Wizard’s Craft Guilds to build a small banking empire to Kings.

Doge Uberto Colainni has a pirate problem. He’s always had a pirate problem. Before, they could be bribed to pay back a cut to him of what they stole but they’ve not paying up and they’re putting a dent in the profits. Normally, he would send out the Bavoria fleet to take care of the problem but King Stephen II is in to him for 1.2M gold plus interest from the last little adventure in War five years ago. The Doge knows the good King has an entire kingdom of Knights and brave adventurers who might be getting the hot idea to come adventuring right at him. The Doge prepares a courier and sends a message. In returning for forgiving a bit of that war debt – debt the good King will run up again – the Doge will send his Knights off somewhere that will keep them occupied for a while.

The King’s Men fan out across the Kingdom and position themselves in Inns offering adventure. An old man wearing the King’s colors tells a thrilling story around the fireside of sun drenched cities and horrible pirates and a chance for glory and stuff. The King himself is calling adventures to join the cause. The adventurers can keep any booty they find! All the adventurers need to do is rendezvous with the contact in Bavoria – here’s a name – in a month’s time and they can take part in this, well, let’s not call it a crusade, really. A fight for Chivalry. Pirates are evil! Rar pirates! Go good! Fight evil! Go over there so you stop draining our coffers!

And a bunch of Random Encounters later, the adventures find themselves in Bavoria. A city of money! A city full of crime! A city where scoundrels will roll the party blind! But it’s also a city of wealth, of wild parties, of politics, of murder, and of ancient ruins the party can go through and level in if they are a little under-leveled. The Guild of Diviners will identify magic items for quick cash but then we’re back to the problem of actually selling magic items. It doesn’t help that the diviners are also in the pocket of both the Thieves Guild and one of the other great families of Bavoria, the Campise, who is standing up a competing Thieves Guild-slash-Financing House, and now they know the party has magic items and of what size and what kind and from where… but first, pirates.

Sure enough, Knights and Lords from all over King Stephen II’s kingdom filter into Bavoria. They feted on the backs of peasants all the way from their capital city here. And they are ready to kill pirates. Oh are they ready to kill pirates. Is the party ready to kill pirates? The NPC knights are all about killing pirates!

First problem: no one can take horses. The boats don’t have enough room for all the armor and the squires and the mercenaries and the adventures and tents and supplies and horses. The boats are only so big. The horses must go, and due to a sudden glut of horses, they’re going at half price. Now Bavoria has a lively but short-lived trade in horses! A win for everyone!

Second problem: the clerics of King Stephen II’s Kingdom are slightly different from the clerics of the Republic of Bavoria so no one agrees on the right blessing. After an altercation and possible cleric-and-paladin fist fighting, the party has a problem to solve. They can solve this however they see fit, including allowing the clerics to hit each other until they’re unconscious and then have the party cleric bless the mission. And clerics? They’re mean.

Finally, everyone boards. The boats cast off! They float around on the sea for a while. They fish. They have fights on the sea with pirates! And the party lands on shore surprisingly fresh.

Here’s where maybe someone should have asked a few questions. The Doge of Bavoria did not have King Stephen II or his Knight’s best interests in mind.

The pirate generator is an enormous walled city surrounded on the shore by a river and otherwise surrounded with desert.

If the party thinks to ask no, no one brought any siege equipment. Why would we bring siege equipment? What those walls?

The NPC Knights, however, did bring many barrels of wine.

The pirates, knowing the Doge was getting irate, called their buddies who called their buddies and they have bored warriors and mercenaries, too. Now just off the city is an army of 30,000 heavily armed orks on horseback.

The orks on horseback don’t seem interested in attacking. They mostly seem interested in sitting just out of range and laughing.

Also Knights? In the desert? In heavy plate armor? Without horses? All those good Knights and Paladins aren’t going anywhere fast.

This is where the party is at. There’s all sorts of interesting possibilities the adventuring party can pursue:

The party can be super clever, figure out a way into the city through some ancient sewers and destroy the pirates from the inside. The city is not a normal city full of people kept hostage. It truly is full of nasty goblins, orks, evil demi-human races, hobgoblins and the occasional bugbear. Meanwhile, outside the city walls, the NPC Knights will try to make a single siege weapons out of driftwood (which burns) and mostly die of heat exhaustion in their metal cans.

The party can have a throw down with the champions of the ork army after sets of skirmishes. In some twisted ork tale of honor, if the two champions of two armies meet, the one set of champions who survives is the winner of the war. Winning will disperse the ork army.

The party can attempt to oust the useless head of the NPC Knights, one of the erstwhile Dukes but not the Duke of Shoral he was too smart for this, take over the army and actually hold a useful siege. But they won’t get any respect unless their head is also Nobility of King Stephen’s Kingdom.

The party can get back on boats and fight the pirate menace on the seas. Sooner or later they will meet a Pirate Boss who will give them an epic fight.

No doubt there’s all sorts of interesting exotic places to explore off the beaten path: other ruins, interesting trade cities with strange cultures, and more clusters of pirates.

The head of the NPC Knights, a Duke of Canet, who claims descent from elves and the royal line of Kings, has little interest in anyone’s advice. He will bat it away with one hand and drink hot wine under a hot sun in another. To him, this is a big party and the longer it lasts, the better. The siege entertains his men and occasionally one of the small skirmishes results in booty. He has to milk this siege in a far away land for all it has.

Regardless, the NPC Knights after a long time of hanging around in tents with bright banners, screwing around, getting each other killed in skirmishes, and generally failing to do anything useful, will eventually tear down their tents, get on boats, and go home. Unless the party manages to take the city and defeat the pirates themselves, the Knights return to Bavoria totally and completely successful in their own minds despite it looking pretty, well, like a huge failure.

But someone wins in all this. Who wins?

The Doge wins because regardless what happens, the pirates back off a bit giving him a great financial victory which he will use to hire assassins and off members of rival wizarding families.

The pirates win because they still have their big army, their pirating base, and they made a bunch of knights look like jerks. The tiny war thinned their numbers so the pirates back off for a bit but check out the recruiting propaganda they get in return!

The party wins because they get to go on cool adventures and take stuff.

King Stephan II gets rolled. Sure, he gets his Knights out of his Kingdom for a while but the Knights didn’t return with much he could put into his treasury. He’s still in debt to the Doge. And his neighbor is still having its own civil war problems and can’t come fight him. But the Doge is thinking of going to war with his neighbor, the Glorious Republic of the Iron Isle and could use some Knights. He’ll be happy to forgive some debt but King Stephen II will have to arm them…

The moral of this long drawn out story: Maybe the old man in the inn giving out adventures doesn’t have the best of intentions. Also, more importantly, wise rulers keep a constant war at the edges of their kingdoms far away from their central cities and bases of power. Campaigns work best when they send adventurers out to the far reaches of civilization. D&D is essentially a western.

As you can probably guess, this was all based on real history of the Crusades which were exactly as dumb as this. And every bit as successful.

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While killing an ogre for the local Baron for a quick pickup of 100gp, the party offs the ogre’s buddy, a nasty little goblin. This guy was a real jerk. Once he was good and dead – the fighter stabbed the goblin extra for good measure – the party did what adventuring parties do. They rolled the bodies. Among the handfuls of copper pieces, a few unusable weapons and a convenient cache of crossbow bolts, the party discovers the goblin was wearing a pair of Boots of Striding and Springing.

For whatever reason, the party decides it doesn’t want to keep the boots. Perhaps it is a matter of taste. The style is out of fashion. The size is too small. Also, as magic items go, boots of striding and springing are on the low-end of the interesting scale. Regardless, the party takes the boots to the nearby peaceful peasant market town to unload them as one does with unused magic items.

The local cordwainer won’t accept the boots of striding and springing. The cordwainer, a member of the local shoemaker’s guild in good standing, doesn’t recognize the boots as magic but he does recognize them as a different make than other boots made in the region. Good quality, good make, but they’re not his nor one of his fellow guildmates so he cannot resell them. He is not authorized to buy and sell foreign goods and if they’re left in his shop, he’ll get found out by the guild for hoarding strange makes of highly unauthorized footwear. There’s a price list. He likes being part of the guild, see. They help him and his family out when he’s down. His father was part of this guild. His grandfather was a grandmaster of the cordwainers of the peaceful peasant village. And he doesn’t want any trouble. Besides, he only pays in script and not in coinage. The party needs to move along.

The local merchant doesn’t recognize the boots, either, but he recognizes them as magic immediately on inspecting them on the counter in his small shop. The wizard’s craft mark is on the inner sole. See that right there? These are wizarding shoes. Great magic in wizarding shoes. The merchant’s guild in this region isn’t permitted in its charter to resell strange, foreign wizarding shoes. They banged this charter out so the merchant can sell commodity goods here and the Baron stays over there where the town would like them and the Baron, well, he takes interest in these sorts of things. Maybe the party took them off a wizard? That’s a problem right there, too. The merchant can’t pay for strange foreign wizarding things in his shop. Brings nothing but trouble. Besides, the town mostly works on script, ledgers, loaning and mutual debt. The merchant can only pay in Bob the Baker’s bread. Do you like bread? Bob’s bread? Fantastic.

Forcing the merchant to accept the boots unearths the hard reality that the Merchant’s Guild of the town is also the Judge’s Guild, the local Mafioso Guild, and the Government Guild. This merchant? He’s also the Mayor. And the Head Judge. The merchant will call in his friends and his friends will make sure the party doesn’t sell no weird, foreign, and possibly evil wizarding shoes in this town. We won’t kill you right here and now because of the ogre business but maybe it’s time to go. The locals are not much when it comes to fighting but leaving an entire town murdered over a pair of boots – there’s a slippery slope to neutral evilhood. The party’s cleric might be irked.

Getting the local Baron involved brings up all kinds of ugly questions like: “Why are the lower folk walking around with a pair of magic boots?“ And then the magic boots will belong to the Baron because he needs to go on campaign and he doesn’t have magic boots. Now he does. Yours. Not a great plan. Great guy until someone shows up with some magic items and then not such a nice guy any more.

Barding up the merchant or pulling out some merchant background can get a bit of “I know a guy who knows a guy who knows a guy.” Maybe there’s something the merchant needs for a bit of favor. Besides, the guy trades in favors all day. The local merchant is not of any help but there might be an upstream reseller. Here’s a bit of a written introduction and a rough schedule for a Faire that moves around a number of cities. Nomenally that faire sells cloth but an entrepreneaur can unload a pair of boots if the buyer is right and the place is right and the money is right.

Calling down on God or Gods is a thing that works because if there is anything a merchant needs, it’s a blessing to help him move those more mundane items in his shop. But he still doesn’t handle foreign magic goods and he can only pay in what he owes to other townspeople.

Cutting the inner soles out of the boots to remove the wizard’s mark and leaving them with the local non-guild affiliated peddler with his jingle jangle wagon of assorted goods for a few copper will get rid of them quick but these boots are worth some serious scratch. Always an option but no adventuring party is going to get rich off filing the serial numbers off magic items and unloading them on movable consignment stores.

No one in the town is going to buy the boots the local head cleric explains to the party on their way (hopefully) out of town. And no one wants them. These are good people. Godly people. People who tithe regularly to their local Temple. What the local head cleric, who is one of those nice guys affiliated with one of the local Gods of home and hearth, wants is the party to take the boots and leave. They will bring nothing but instability to this nice little community. If there’s anything the Gods want, its stability.

A group of towns who want to become cities situated on ancient trade roads hold a rotating open market. What it is, who hosts, and where it is held depends on the time of year. The external appearance of the Faire is selling well-known commodity goods: one week is cloth, another is spices, another leather and other durable goods. Merchants travel over incredible distances marked with the occasional Random Encounter to make it here to unload from all over the known world and over it all a rich and powerful Lord who makes it happen with the guarantees of security and law. It’s his Law but his Law is he gets his tax. As long as no one sets the entire town on fire and brings the Lord into it, he’s fine with whatever nonsense happens.

No one sells magic items in the open here, either, but the party can lay hands on some seriously upgraded pieces of mundane equipment if necessary. At night, behind the tents and in the bars, people settle their accounts and the interesting goods exchange hands.

By knowing a guy, having a letter of introduction, getting the right people drunk, surviving a few fist fights, and generally running around depraved, it’s possible to find the magic items broker. The party will bump into a bunch of other guys, too. Nothing is ever simple on the quest to unload a pair of slightly magical boots:

Someone from one of the Wizard Craft Guilds is attending the Faire looking for the same sets of background deal brokers to unload their magic items into circulation. (How else do they make their way into dungeons and random treasure tables?) The Wizard Craft Guilds aren’t like a small peaceful peasant village Shoemaker’s Guild. These are guys with money, muscle, and agents to move their merchandise. And these aren’t the Wizards themselves, of course – no self-respecting Wizard is going to come out of his tower to sell at some Faire. That would mean getting dirty. This is a broker’s broker with his own set of thugs. And they want to know why this party is selling strange, foreign magic boots with a different wizard’s mark than their Guild into circulation.

Is the party now magic boot-making competition?

Is there a collect and resell effort from foreign points going on to dilute the list prices of magic items?

Are the local wizards of the Wizard Craft Guild being scammed?

Maybe what the party needs is a visit from the broker’s local group of armed friends, in the cover of darkness, behind the bar. Because while the party may not have to go, the boots certainly do.

The black market gets whiff there’s some action in the magic items area and, unlike the rubes back home, these are guys who know how to move magic items and get them into the hands of discerning dealers. Sure the party might be running from the thugs behind the Wizards Craft Guild but here’s a friend – really! a friend! – who only wants to get the best price for the boots for his quiet, discerning client. This is safe. This is clean. No Guilds involved at all except for Ours but you don’t need to know about that. This will move the boots and sell them to a discrete buyer. The Necromatic Arch Lich and his Legions of Terrifying Evil who simply need high quality footwear as they trample on the necks of the local populance. You know how it is.

Running amok away from the thieves’s guild and the wizard craft guild, the party draws the attention of the local Merchant’s Guild who both try to turn a blind eye to all sorts of shenanigans but if inns start getting burnt to the ground, they’re both going to get wary. Luckily for the party, the local Merchant’s Guild is on a whole different playing field than the local Merchant’s Guild of the small town. These guys finance entire armies for rich patrons. They have their own set of mercantile laws that have nothing whatsoever to do with local Law, or the Lord’s Law, or laws from the local Temple. These guys are judge, jury, executioner, and the entire local government. We leave that for now, because the Merchant’s Guild wants to see if the party lives. If they do, there might be something in it for them.

And after lighting some bar on fire while running out, the party hooks up with their guy. They have wizard guild thugs after them. Black market mafia thugs after them after breaking their deal to sell the boots. They got beer all over their new leathers. Letters of introduction are exchanged. In a room in quite another inn across town, the magic item broker looks at the boots, looks at the wizards mark in the sole, and he tells you his fee for moving the boots is 37%. At a list price of 5500gp, he’s going to take a little over 2000gp from the party for the price of taking those boots off the party’s hands. Good magic item laundering service is expensive.

In a time of craft guilds, merchant guilds, organizational guilds, nobility, and wizards in towers protected by armies of thugs, it’s hard to move foreign merchandise. No one wants to accept the risk of explaining where the item came from. And all the rich guilds have their form of muscle and protection. This is all to say, one can get mileage out of a pair of boots rolled off a dead goblin. And maybe in the end it is easiest just to pull the soles and unload them on the peddler. It’s cheaper that way.

The Faire is based on the Champagne Faires, a thing that happened before the rise of the Hanseatic League and a tribute to the absolute determination, in the face of Kings and Guilds, to turn a buck.

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The party stands before the local Lord of the small town they’re passing through and responding to an ad: Kill the local ogre in the hills for 100 gold pieces! George the Ogre menaced the roads leading into the Lord’s holdings and villages so the Lord wants George gone. You, the Murder Hobos, who breezed through go hey, we have weapons, we have skills, we have experience points, we can take out George. And you do! The local Lord hands out the 100gp (along with the party getting whatever experience points an Ogre was worth) and the Murder Hobos hobo along.

Where does the 100gp originally come from?

Assuming the fantasy world our Murder Hobos inhabit is plausibly “Vaguely Western European Medieval” with some hand waving about elves, 90% of the population works in agriculture. Sure expensive magic could make agriculture marginally more effective for the whole population but the structure of most of the countryside are manors of Lords overseeing combinations of bonded villeins and free peasants working the land. Even elves need to eat – or maybe they don’t, but people do. Dotting along the road is the occasional inn and a few small market towns with functional marketplaces – and these are where our friends, the Murder Hobos, hang out.

Unless the Petty Lord in question owns a mine of some sort, he has few options to raise that 100gp:

Squeeze the Peasants. Why bother to pay that 100gp himself to get rid of that ogre when his peasants surely have a few coins stashed under the floorboards somewhere? This is what Sheriffs are for. Go squeeze the villeins and free peasants – those free peasants are always good for cash. Ever wonder why in old 1st Edition Dungeons & Dragons the cash rewards would be in weird denominations? As long as it all adds up to 100gp, who cares the Lords squeezed the peasants a few copper at a time?

Raid a nearby village. Why squeeze one’s own peasants, who will surely resent being squeezed, when one can go burn down a rival’s village and force the peasants to cough up 100gp at swordpoint? It really only takes the few buddies that live with the petty Lord, some horses, a few swords, and some flasks of wine… It’s one thing to knock over a few peasants, and it’s another thing to take on an ogre. An ogre is dangerous business.

Squeeze the hostage. Hostage? What hostage? Where did a hostage come from? Surely at some point the petty Lord went on his campaign with his Lord. And that guy has a Lord above him — a Duke or Earl, perhaps. And that Duke got lucky on his last campaign when knocking over some other peaceful peasant villages. The petty Lord, with supreme luck, managed to take out a rival Knight and now has said rival Knight hanging around eating all the food. But the rival Knight’s family is another set of Lords with their own peasants to squeeze so our original magnanimous Lord with the ogre problem sends away for a bit of financing. And here it is.

Our party goes and rolls the ogre. Possibly the ogre has some goblin friends, maybe a few orcs, and maybe if he’s a high charisma ogre a bugbear. (Bugbear!) The party rolls the enemy, collects a few trinkets, and saves the village. Huzzah! The peaceful peasant village is saved! They are heroes! The petty Lord gives them 100gp to go away because he needs to get back to the pressing business of ensuring this year’s crop comes in to cover all his costs for his next year’s so-called war with his Lord.

And the murder hobos do go away because they have 100gp burning a hole in a pocket and it needs to turn into stuff.

Medieval agrarian societies experienced little inflation over long periods of time. Little money entered into the macroeconomic system to force prices to fluctuate and the pernicious guild system held prices artificially static. The cost of wheat was the cost of wheat. For prices to rise, someone dumps buckets of cash on the society as a whole. Serfs had little money because they were serfs, Knights (petty Lords) had little money because they had to pay for the arms of war and kick up to their Lords… one had to crawl up the hierarchy before the murder hobos find concentrations of wealth.

But then a group of murder hobos would hoover 100gp out of one small community, find the nearest marketing town, and dump it all there like insane agents of the Invisible Hand. 100gp didn’t just buy drinks, it bought the entire bar. The best thing for the entire community is if the murder hobos took their money and left. Talk about acts of redistribution.

Since economic pressures put on groups of elves and dwarves in a Feudalistic society who take up arms to wander the country side and kill ogres interests me, I can game out some of the our party’s choices after spending their 100gp on whiskey.

1. Roll over to the next Lord and take another well-meaning good-aligned job they heard from the previous bar to rescue another peaceful peasant village. The process starts anew, except this time the murder hobos ask for250gp instead of 100gp because the party leveled and they have more expensive equipment and reagent needs. They continue along like this until they fight the big boss at the end of the module and destroy a small country’s carefully balanced economy by dumping the treasure on a small marketing town. Perhaps once the adventure completes, the murder hobos become an upgrade: the murder mercenary company. Why take out goblins when one can take out towns and knock over petty Lords themselves? Cut out the middle man.

2. Climb up the ladder from petty Lords to big Lords and Churches. If anyone has money, it’s those local Temples that dot the countryside squeezing the local free peasants and moderately wealthy landowners for their cash (since they can pony up and don’t have their own private shrines.) You Clerics you with your wealthy Sanctuaries and need for adventuring teams to go do things. At higher levels, the murder hobos can shake down people who shake down people who squeeze the peasantry en masse. Not only does it make more money and destabilize an agrarian society faster, it’s more efficient for higher levels!

3. Get thee to a city. And hold onto that thought.

Once the petty and not-so-petty Lords get rolled a few times by the murder hobos, they have their own choices because they need to get their wheat to market, they don’t know how to figure in inflation, and seriously they have bills to pay and these guys need to move on. They can (lists of threes! lists of threes!):

1. Buy another murder hobo company and sic them, for another 100gp, on the first murder hobo company in hopes of mutual annihilation.

2. Militarily mobilize against the murder hobos – oh thank you for saving us now please go far away and stop hitting all the manors on the road for jobs please. Maybe raising troops and mass mobilization is the best way to get right of the plague of lawful good adventurers who just want to help the poor and the oppressed against the legions of evil?

3. Join ‘em. It’s more lucrative to murder hobo rather than run lands as Knight So and So of SuchandSuch. Grab the sword, leave the gun, take the cannoli and surely they need an NPC fighter! Who doesn’t? There’s a Storm Giant menacing a village over the rise.

And now our, oh, 7th or 8th level murder hobo group who has saved many peasant villages now have an entire chorus of ex-petty Lords helping them to right the wrongs while they ravage the countryside, and some Duke or Earl or even King will get smart and point them at their enemies for a bribe of, say, 10,000 gp ganked no doubt off the back of a hundred thousand peasants paying taxes…

Murder hobos are no good for a fine Western European Medieval economic climate full of elves. So much for the long-term economic stability of the Hobbits of the Shire.

Cities – small, filthy and few as they are – are the only civic and economic structures with enough wealth to support the rapacious needs of the average, healthy, constantly leveling murder hobo. A 100gp disappears into the cities dark streets like water after rain. Guilds extort from one another. Landed Churchmen run the heads of their Temples out of Cities. Governments make their headquarters. These are the guy with hard cash. Where they got the hard cash is of no concern – they have hard cash. Never mind with landed nobles. Those guys are broke. There’s some Guild there who has long term grudges with another Guild and wants to get their pay and all they need is a group of murder hobos who have leveled up siphoning all the money out of the countryside.

Imagine the rogue class of the Auditor who works for the Guilds with the Guild Artisan background who makes sure that now the team is part of the City they pay their kickbacks to the Guilds themselves….

When Guilds don’t have enough money, some Lord of a rich city state who doesn’t bother with such things as lands and rents but in real things like proto-banks and ports needs to have a rival sacked. Here’s a scroll of fireball! Gratis! Go sack. Hope you don’t come back!

Given an infinite amount of time and actual economic pressures, all adventuring groups become neutral evil.

There’s a lot to this subject. This doesn’t even touch money-lending and usury and rents. This is a time with no real banking – where do the murder hobos store their cash? – and few mints churning out coin. Lords pass off murder hobos based on IOUs they never intend to pay and then other Lords who will call those in. Backstabbing guild politics of the highest order and free peasants willing to use murder hobos on their climb by their fingernails up the economic ladder so they can buy themselves a title. And this is just what is rolling around in my head. The murder hobos rely on an invisible system to support their need to Do Good: the wealth of the churches, the rent taking of the lords, the control of the guilds, the networks of small market towns destroyed in their wake by overindulgence of beer.

The White Company is the best of real history rapacious and completely gonzo mercenary adventurers who had some fun in 14th century France and Italy. A Distant Mirror by Barbara Tuchman describes the White Company and the role of mercenaries in medieval society in loving detail.

Anything on the Black Death is good for exploring what happens when disease upends a perfectly good Feudalistic system. The history of printing gets one into guerilla warfare tactics between guilds and free enterprise (printing was never guild controlled) and the length they will go to blowing up each other. Seriously, the history of printing and the printers wars with keeping out of guild control is the best historical story no one knows about.

Debt: the first 500 years has a chapter on Western medieval economics in detail and describes what happens when one dumps huge amounts of liquid cash on a low cash velocity society. (Hint: massive hyperinflation –just ask Spain!)

I am currently reading the Story of England by Michael Wood which describes life in a Medieval and Renaissance society in loving, personal detail. Also, academics are jerks. If you thought monasteries were bad they are nothing compared to a small Liberal Arts college in 1300AD.